


we ain't ever getting older

by shippindales



Category: Teen Wolf (TV)
Genre: Blowjobs, Bottom Stiles Stilinski, Ends with feels, FBI Agent Stiles Stilinski, Lawyer Jackson Whittemore, M/M, Oneshot, Rimming, Song: Closer (Chainsmokers ft. Halsey), Spanking, Top Jackson Whittemore
Language: English
Status: Completed
Published: 2020-05-17
Updated: 2020-05-17
Packaged: 2021-03-03 01:48:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,382
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24226870
Author URL: https://archiveofourown.org/users/shippindales/pseuds/shippindales
Summary: On a rare night off, Agent Stilinski runs into an old flame at a hotel bar. Jackson looks damn good in that three-piece suit, and they've got a lot of time to make up for.
Relationships: Stiles Stilinski/Jackson Whittemore
Comments: 10
Kudos: 262





	we ain't ever getting older

**Author's Note:**

> Gift fic for Cailee jacksonstilinskis that was hatched from a post four+ years ago where she said that Closer was a totally Stackson song. I offered to write it and then vanished like dust on the wind for a million centuries. But here it is, to kick off Stackson Week 2020!!!

It was the kind of atmosphere that Stiles liked, when he needed to unwind for a bit. It wasn’t a sleazy hole in the wall type of place, nor was it too ritzy or stuffy for his tastes. Ease in the air, good ambiance with the dim lighting and low music, bartenders who got down to business and knew when you didn’t need a conversation, and a decent crowd. Not too bad, all things considered, for a hotel bar.

He nursed his gin and tonic as he pulled lightly at his tie, loosening it enough until it dangled from his neck freely while he unbuttoned the top two buttons of his shirt. Wearing a suit would never grow on him, regardless of how his partner insisted that it gave them _stature_ and _authority_. Miller could blow it out his ass, being federal agents gave them all the stature and authority they needed. But damn, he’d kill for jeans and a t-shirt every once in awhile. He’d have to beg for an undercover op next.

It was his fourth night at the hotel in Denver, and the stakeout was getting stale. Miller had insisted he take a night off, even called in a reserve agent just to take his spot so that he could blow off some steam. The night was young, and Stiles figured he had a multitude of options ahead of him for where his evening could go.

That was, until raucous laughter started up from the table across the other end of the sparsely populated bar, and Stiles rolled his eyes at the group of well-dressed men that sat around it, their chatter rolling over him until he looked a little more carefully, and caught a very familiar eye.

He nearly spat out his drink, and the glass clattered to the bar noisily in front of him, drawing the attention of the concerned bartender and a few patrons nearby. He waved them off, dabbing at the spill that had splashed onto the front of his shirt with a bar napkin, before he looked back over, and couldn’t make eye contact anymore. He flushed scarlet, embarrassed at the extra attention, and stared at the wall before tipping the glass to his lips and downing his drink in a few solid, full gulps. He signaled for another in answer to the bartender’s unspoken inquiry as she raised an eyebrow and motioned to his glass.

An hour went by in seemingly seconds as Stiles’ thoughts raced. It was obvious he didn’t want to reconnect, or he would’ve said something. Or maybe it was just the crowd he was with, and he didn’t want to draw attention to anything. What if he’d already left? Stiles couldn’t see the group of men clearly from where he was sitting, and a few of them had been in and out, though he was pretty sure he knew which one was him... he frowned. He’d lost sight of him. A dull ache started to form in his stomach that was unrelated to the buzz from his third drink.

“You know, all the ways I pictured we might run into each other, and this wasn’t one of them,” the smooth voice purred in his ear, and Stiles sat bolt upright, spinning around to face him. Jackson fucking Whittemore, in all his three-piece suited glory, grinning like the cat that ate the canary.

Stiles froze for a moment, his mouth hanging open, before Jackson’s words sunk in. He looked across the restaurant and noticed that the remainder of Jackson’s table of companions was filtering out the door, and he turned back with a sly smirk on his face. “Too shy to introduce me to your fancy buddies over there? What are you guys anyway, stock brokers?” He raised an eyebrow, looking Jackson up and down.

Jackson didn’t miss the roving eyes, though his shirt was still buttoned up tight and his tie in place, unlike Stiles. He looked the other man up and down himself, before taking a swig of his beer. “We should maybe reintroduce ourselves, considering it’s been awhile. Jackson Whittemore, Esquire.” He held out a hand to shake, a proud smile on his face that put butterflies in Stiles’ stomach.

He gripped it tightly and shook, growing goosebumps on his arm in the process, before pulling out his badge and flipping it open. “Agent Stilinski. FBI.” Jackson’s eyes widened in surprise, and Stiles smirked. “Yeah, I know, I was the hot gossip at our five-year reunion. Which you missed, by the way.” He pointed accusingly at Jackson, his finger poking him in the chest. Jackson didn’t shy away from the contact, leaning over the bar next to Stiles and resting his drink on a coaster.

“Yeah, I missed it. Law school beat the shit out of me. I don’t know why I ever decided to follow in my dad’s footsteps.” He shrugged. “But it’s been a pretty good life so far. And uh, the academy’s done good things for you.” He raised an eyebrow, admiring the way Stiles’ form had filled out since high school. And Stiles knew, he’d definitely grown into the gangly limbs and awkward proportions since he was a teenager.

Not that it hadn’t been a struggle. He’d spent his first few weeks at the academy feeling like he was going to die, but the physical training had gradually honed him into a toned, lean version of himself that he never thought he’d see in his younger years. Regardless, Jackson’s obvious attention to it had him flushing slightly.

The unspoken tension filled the air before Stiles took a deep sip of his drink, setting it down carefully. “You never kept in touch,” he pointed out. It was casual, but his tone implied something deeper. Jackson stared at him, noticed the way Stiles’ eyes wouldn’t meet his gaze.

“Didn’t deserve to,” he retorted, which drew a look of surprise from Stiles. “What? I was an absolute ass in high school, dude. And probably even more of an ass in undergrad.” He shuddered. “I’ve grown up a lot. Obviously you have too. But I wanted to be... different, when I eventually got around to reconnecting with everyone, especially you.”

_Especially you._ And weren’t those pretty words to come from an equally pretty mouth. “Yeah, you were an ass in high school,” Stiles acknowledged, though the response from Jackson was a look of more guilt than he’d been intending to inflict. “But you made up for it.”

The implication turned back time to groping hands, shuttered up in Jackson’s bathroom during a party, mouths and limbs and hardness, heat and release— The blush was equal in both their cheeks. It wasn’t a single occurrence, they had quite the history over the last few years of high school.

“I remember,” Jackson muttered, the barest hint of a smile playing on the edges of his lips. “I didn’t know what I was doing then, though. And I was a dick to you about it. You know, when things got more... involved.”

When feelings got involved. Right.

Stiles shrugged it off. Long since passed, and long since forgotten. His attention instead turned to the earlier part of what Jackson had said. “So you know what you’re doing now?” he inquired, and his amber eyes were peering up at Jackson through those thick lashes that always set him off when they were younger, and god damn were those memories coursing through their veins and making them both feel alive, thrumming to the accelerating tattoo that their pulses set.

Jackson gripped Stiles’ tie, pulling him forward forcefully to capture his lips, ignoring the wandering eyes from the bartender and other patrons, who probably thought they were moving a little fast for a first time meet. He felt Stiles gasp quietly underneath him, the heat pooling in his gut as Stiles’ tongue flicked out gently to trace his bottom lip. They separated, breathing heavily, before Jackson pulled him by his tie a little further, to lean over in Stiles’ ear once more. “Want to find out?”

Stiles dug into his wallet, slapped a fifty on the counter and downed the rest of his drink. “Let’s get out of here,” he murmured, and Jackson followed him out the door before pressing him against the brick wall, humming into his mouth as their tongues danced. “Easy, tiger,” Stiles chided gently, grinning as Jackson nipped down the side of his jaw to his neck.

“Got a lot to make up for,” Jackson muttered against his skin, sucking a deep bruise into Stiles’ collarbone as he shoved the offending fabric of his dress shirt aside. His hand slipped into his pocket and came back with his car keys, clicking the remote. A black Range Rover beeped from the isolated corner of the parking lot, and Stiles looked before rolling his eyes.

“The Rover doesn’t surprise me, Mr. Porsche,” he teased, laughing as he danced away from Jackson’s needy hands and lips, making for the rear passenger side door. “ _Esquire_ over here flashing what he can afford.” There was no venom in his words, only joking praise.

“Why are you getting in the back?” Jackson asked, confusion knitting his brows.

“Because so are you,” Stiles retorted, and the mischievous grin spread across his face as he opened the door and hopped in. The grin that brought the memories surging back as Jackson hopped in the backseat from the other side, their mouths clashing urgently as Stiles tugged on Jackson’s jacket, discarding it into the front seat with little regard.

It wasn’t long until their shirts were open, and Jackson was pressing their chests flush together, relishing in the keen that came out of Stiles at the feel of skin on skin. He nipped down Stiles’ neck to drag his tongue along his clavicle, biting down sharply.

Stiles yelped, but felt himself stiffen completely, because yes, _this_ was what he missed. The way Jackson never treated him like he was breakable, trusted him to handle it, and it was something he’d been missing for a long time. He didn’t get around much with his busy life and his federal job, and he felt like a tightly coiled spring finally given the freedom to release.

The way Jackson grabbed his hips bruisingly, like Stiles’d fall through to the center of the earth if he loosened his grip, lit something in him, and he pushed Jackson’s shirt off his shoulder, admiring the tribal tattoo design he found there. He sank his teeth into it, satisfied with the way Jackson threw his head back and _moaned_ at the contact.

“Stiles,” he interrupted, but Stiles paid no mind, kissing his way down Jackson’s hairless chest as he pawed at his hardness through the front of his suit pants. “As much as I’d love to fuck you in my backseat, I think we need a bed.”

Stiles came up for air, after kissing down Jackson’s abdomen. He shrugged his shoulders, nipping at Jackson’s lower lip lightly. “Fine then, Whittemore. Take me home and take me to bed.”

The door slammed behind them minutes later, after Jackson had broken nearly every traffic law in the state. He yanked at Stiles’ shirt impatiently, pulling it off of his arms before their mouths were back in contact, shrugging off his own shirt as their clothing fluttered, forgotten, to the floor. Searing heat and the clash of rushed, hurried teeth filled Stiles’ consciousness, as Jackson’s hands roamed down his sides and slipped underneath his waistband, palming Stiles’ ass impatiently.

“Fucker,” Stiles growled into his mouth as he arched his back into the touch. Jackson reached down and grabbed him around the waist, hauling him up until Stiles’ legs wrapped around his waist instinctively. He threw the other man unceremoniously on the bed after shoving into the bedroom, and Stiles collapsed in a pile of limbs before turning onto his back, sighing gently. “Your mattress is comfy,” he complimented, a stupid grin slapped across his face as he shimmied out of his pants.

“My law school roommate in Boulder ditched the last month of rent. I changed the locks and stole his furniture.” Jackson’s belt whipped off lightning quick as he shoved his own pants and underwear to the floor, his cock springing free of its cloth prison. He hissed as it met the cool air, and Stiles licked his lips as they collapsed back together, hands and mouths fumbling deliciously.

After a few moments, Stiles scrambled down the bed to swallow him to the hilt in one fluid motion. Jackson hissed as Stiles’ tongue flicked out around the base of his shaft as he took him into the back of his throat. “Jesus _fuck_ , your mouth, Stilinski. Missed it so much.”

Stiles pulled up and off of Jackson’s shaft with a wet pop, before smacking it lightly against his cheek. “Guess you’ll just have to make up for lost time then.” He ran his tongue from base to tip, swirling it around the head before delving back down, and Jackson pulled his own hair to keep from yelling to loudly at how fucking incredible it felt.

Stiles hummed around his shaft, bobbing to the base and back to the tip to swirl his tongue in the way he knew drove Jackson nuts. The humming sent deep vibrations through Jackson’s flesh and he let out a ragged, broken moan.

The taste and feel of him bombarded Stiles with memories of the first time he’d ever sucked Jackson’s dick, denial radiating through the other boy even as he’d twitched in anticipation, letting out a rough breath as Stiles finally took him in his mouth.

_“Do you like it?”_

_“Shut up and keep going.”_

Jackson was growing impatient, and he finally pulled himself out of Stiles’ mouth, reaching down to throw the other man further up on the bed, stomach down, receiving a yelp of protest which quickly died on Stiles’ lips as Jackson kissed down his back to his ass, biting sharply into his left cheek. His breath ghosted over Stiles’ hole, and okay, yes, this was a thing that they’d never done together before that Stiles was 120% on board with.

“Are you seriously going to _ahhhhh fucking shit Christ Jesus_ ,” Stiles babbled as Jackson’s tongue flicked out and laved at his rim like a man starved, both hands palming Stiles’ ass and spreading his cheeks and yeah, okay, Jackson had picked up some tricks since high school. Yup.

His sensitive hole was twitching under the ministrations of Jackson’s tongue, and Jackson hummed as he pressed his tongue inside the taut ring of muscle, eliciting a sharp sound from Stiles that he wanted more of. A finger joined his tongue, then two as Stiles relaxed under his efforts.

“God, I can’t believe I’ve never opened you up like this before,” Jackson panted. “You’re so warm and open, so good for me.” His praise was radiating through Stiles’ bones as he pressed his hips back.

“I need you,” Stiles groaned. “Need to feel you again. It’s been— god, too long, not enough, just— just do it.”

Jackson nodded, moving to obey and flicking open the bottle of lube he’d nabbed from his bedside table, spreading it over himself quickly before pressing into Stiles, slowly but persistently.

Stiles’ eyes screwed tight as he breathed in and out sharply, the burn of Jackson’s breach stretching him in a way he hadn’t been in a long time. “Fucking holy hell, forgot how thick you were,” he breathed, pressing his face into the pillow desperately as he rolled his hips back to take Jackson further.

Jackson paused, for a brief moment, to give Stiles time to adjust. That action alone sent a shock through Stiles’ body. Jackson had never been about how Stiles felt, their clandestine hookups throughout high school had always been about Jackson getting off, but this— this was different, and Stiles felt it, felt the consideration and respect.

He responded by pressing his hips back into Jackson, hissing as the burn reignited but slowly began to dissipate. “Move,” he commanded, and Jackson obeyed.

And this, this was what Jackson had missed the most. “God, the way you look spread out around my dick,” he groaned, fucking into Stiles with earnest, staring down at the way Stiles’ hole gripped his girth each time he slid out.

“Shit, Jacks,” Stiles grunted, slamming his hips backwards to meet Jackson’s thrusts, all earlier thoughts of tenderness abandoned. “God, I forgot how good you felt in me. It’s been so long. Always so fucking hard and rough with me. _Fuck._ ”

Jackson’s hand cracked down onto Stiles’ ass, drawing a yelp and leaving an angry red handprint. He spanked him again, twice more, three more times, causing Stiles to let out a long, sharp series of moans. “Fucking take it,” Jackson bit out, pummeling into him rapidly.

Stiles’ talk devolved into senseless syllables and nonsensical babbling as he felt the pleasure coiling in his gut. “Mmmm, f-f- _fuuuuck,_ I’m gonna— I’m close, I—”

Jackson halted, reaching down with both arms and flipping Stiles over onto his back in one smooth motion, bending his head to bite roughly on Stiles’ bottom lip as he pushed back in, holding him around his waist with his legs in the air as he jackhammered in at a punishing pace. “Want to see it,” he panted against Stiles’ lips. “Want to see you let go, see how taken apart you are when you come.”

Stiles came with a shout, spurting copiously all over his chest, his eyes screwed shut and fists tangled in the sheets. Jackson followed him over the brink, moaning loudly as he shoved to the hilt and spilled himself inside Stiles.

Collapsing on the bed next to him, they both laid for a few moments, Stiles’ head lolling over onto Jackson’s shoulder. Their breathing was still heavy, though their pulses began to slow after having finally reached their peaks.

“So,” Jackson began, running his finger through the mess on Stiles’ abdomen and popping it into his mouth before pulling it out with a pop. Stiles’ eyes followed him, blown wide and dark. “Made up for lost time?”

Stiles nodded, grinning wildly as he ran his fingers through his sweat-dampened hair. “It’s a start.”

A start. Jackson nodded, breaking eye contact as a smile spread across his face.

* * *

He traced his fingertips around Jackson’s abdominal muscles absentmindedly, leaning his head into the crook of the other man’s neck. Jackson’s eyes were lightly closed, satisfied after their round the next morning. They were resting quietly, the morning light filtering in through the taupe curtains and spilling warm rays of sunshine across their mostly still forms.

“Would things have been different?” Stiles asked quietly, prompting a soft, questioning hum from Jackson, who kept his eyes closed, but rubbed circles into Stiles’ shoulder with his thumb. “If you weren’t a dick in high school, I mean.” The implication behind it left Stiles feeling vulnerable, and he swallowed it down thickly.

“Maybe,” Jackson admitted, turning to press his lips gently into Stiles’ hair. “I can’t change who I was then. I wish it could’ve gone differently, though.” The unspoken differences echoed in the silence, and Stiles pictured what life could’ve been like, in another world.

“What about now?” he asked, voice uncertain. There was no indication that Jackson had wanted this to continue, that it was more than just a rekindling of an old flame, destined to wither and snuff out as it had before.

Jackson was silent for a moment too long before responding, and it twisted Stiles’ stomach up in knots. “What about it?”

“Is it too late?” Stiles asked. He was unable to form the words, unable to ask directly for fear of putting himself too far out there. Something about this just felt like the universe was pointing them in the right direction for once, and he needed to know now if it was never going to happen.

“Do you want it to be?” Jackson asked.

He blinked, the answer clear as day. “No.”

A small smile played at the corner of Jackson’s lips as he looked down at Stiles. “Then it’s not too late.”

The sun’s rays splayed out gently across their skin as Jackson pulled him closer.

“Good.”


End file.
